4-(Butylamino)-3-nitrobenzoic acid → 3-Amino-4-(butylamino)benzoic acid

HRID 2166034Notes

Reaction equation

HRID 2166034 reaction equation
[CH2:1]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[N+:15]([O-])=O)[CH2:2][CH2:3][CH3:4].[H][H]>[Ni].CO>[NH2:15][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:6]=1[NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 28298164-(Butylamino)-3-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 115502333-Amino-4-(butylamino)benzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 50 parts of 4-(butylamino)-3-nitrobenzoic acid and 240 parts of methanol was hydrogenated in a Parr apparatus at 3.105Pa and at room temperature with 40 parts of Raney Nickel catalyst under nitrogen atmosphere. After the calculated amount of hydrogen was taken up, the catalyst was filtered off over diatomaceous earth and the filtrate was evaporated to dry, yielding 43.7 parts (100%) of 3-amino-4-(butylamino)benzoic acid; mp. 158° C. (int. 8).

Workup

  1. filtrationthe catalyst was filtered off over diatomaceous earth
  2. customthe filtrate was evaporated
  3. customto dry

Sources & evidence

ORD record
ord-2add87776fcc412899fe956579092135
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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